Lewis Acid-Promoted Cyclization Reactions of Alkenyl Ethenetricarboxylates: Stereoselective Synthesis of 2-Oxotetrahydrofurans and 2-Oxopyrrolidines

被引：17

作者：

Yamazaki, Shoko ^{[1
]}

Fujinami, Ken ^{[1
]}

Maitoko, Yuki ^{[1
]}

Ueda, Khota ^{[1
]}

Kakiuchi, Kiyomi ^{[2
]}

机构：

[1] Nara Univ Educ, Dept Chem, Nara 6308528, Japan

[2] Nara Inst Sci & Technol NAIST, Grad Sch Mat Sci, Nara 6300192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 17期

关键词：

DYOTROPIC REARRANGEMENTS; INTRAMOLECULAR ENE; PYRROLIDINES; TETRAHYDROFURANS; DERIVATIVES; PRODUCTS; PARTICIPATION; PYRROLE;

D O I：

10.1021/jo401106m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid-promoted intramolecular reactions of alkenyl ethenetricarboxylates and the corresponding amides have been examined. Reaction of ally! ethenetricarboxylates and the amides with Lewis acids (1-2 equiv) such as TiCl4, TiBr4, AlCl3, and AlBr3 gave 3,4-trans-halogenomethyl 2-oxotetrahydrofuran and pyrrolidine derivatives stereoselectively in high yields. The stereochemistries were determined by NOE experiments. Reaction of alkyl-substituted allylic ethenetricarboxylates with Lewis acids gave chloro 2-oxotetrahydrofurans and pyrans. For some alkyl-substituted substrates, cationic intermediates may be formed under the reaction conditions, and rearranged products have been obtained.

引用

收藏

页码：8405 / 8416

页数：12

相关论文

共 58 条

[1] Asymmetric synthesis of an N-acylpyrrolidine for inhibition of HCV polymerase [J].

Agbodjan, Armel A. ;

Cooley, Bob E. ;

Copley, Royston C. B. ;

Corfield, John A. ;

Flanagan, Roy C. ;

Glover, Bobby N. ;

Guidetti, Rossella ;

Haigh, David ;

Howes, Peter D. ;

Jackson, Mary M. ;

Matsuoka, Richard T. ;

Medhurst, Katrina J. ;

Millar, Alan ;

Sharp, Matthew J. ;

Slater, Martin J. ;

Toczko, Jennifer F. ;

Xie, Shiping .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3094-3102

[2] Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2006, 62 (31) :7213-7256

[3] Iron(III)-Catalyzed Consecutive Aza-Cope-Mannich Cyclization: Synthesis of trans-3,5-Dialkyl Pyrrolidines and 3,5-Dialkyl-2,5-dihydro-1H-pyrroles [J].

Carballo, Ruben M. ;

Purino, Martin ;

Ramirez, Miguel A. ;

Martin, Victor S. ;

Padron, Juan I. .

ORGANIC LETTERS, 2010, 12 (22) :5334-5337

[4] 5- and 6-exocyclic products, cis-2,3,5-trisubstituted tetrahydrofurans, and cis-2,3,6-trisubstituted tetrahydropyrans via Prins-type cyclization [J].

Chavre, Satish N. ;

Choo, Hyunah ;

Lee, Jae Kyun ;

Pae, Ae Nim ;

Kim, Youseung ;

Cho, Yong Seo .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7467-7471

[5] 5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via prins-type cyclization [J].

Chavre, Satish N. ;

Choo, Hyunah ;

Cha, Joo Hwan ;

Pae, Ae Nim ;

Choi, Kyung Il ;

Cho, Yong Seo .

ORGANIC LETTERS, 2006, 8 (16) :3617-3619

[6] Efficient Synthesis of 3-Chloromethyl-2(5H)-furanones and 3-Chloromethyl-5,6-dihydropyran-2-ones via the PdCl2-Catalyzed Chlorocyclocarbonylation of 2,3-or 3,4-Allenols [J].

Cheng, Xin ;

Jiang, Xuefeng ;

Yu, Yihua ;

Ma, Shengming .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8960-8965

[7] Switching between Concerted and Stepwise Mechanisms for Dyotropic Rearrangements of β-Lactones Leading to Spirocyclic, Bridged γ-Butyrolactones [J].

Davis, Rebecca L. ;

Leverett, Carolyn A. ;

Romo, Daniel ;

Tantillo, Dean J. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (17) :7167-7174

[8] Diastereoselective Rhodium-Catalyzed Ene-Cycloisomerization Reactions of Alkenylidenecyclopropanes: Total Synthesis of (-)-α-Kainic Acid [J].

Evans, P. Andrew ;

Inglesby, Phillip A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (08) :3635-3638

[9] Recent advances in the total synthesis of piperidine and pyrrolidine natural alkaloids with ring-closing metathesis as a key step [J].

Felpin, FX ;

Lebreton, J .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (19) :3693-3712

[10] Dyotropic Reactions: Mechanisms and Synthetic Applications [J].

Fernandez, Israel ;

Cossio, Fernando P. ;

Sierra, Miguel A. .

CHEMICAL REVIEWS, 2009, 109 (12) :6687-6711

← 1 2 3 4 5 6 →